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Chiral N-phosphonyl imine chemistry: asymmetric additions of malonate-derived enolates to chiral N-phosphonyl imines for the synthesis of β-aminomalonates

✍ Scribed by Zhong-Xiu Chen; Teng Ai; Parminder Kaur; Guigen Li

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
179 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

Chiral N-phosphonyl imines attached by 1-naphthyl group were found to react with lithium malonate enolates smoothly to give chiral b-aminomalonates. Good yields and excellent diastereoselectivity were achieved for sixteen examples. The chiral auxiliary can be readily removed by treating with trifluoroacetic acid (TFA) to give free amino malonates. The absolute structure has been unambiguously determined by converting one of the products into an authentic sample.

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